KR101377467B1 - 알킬페놀이 없는 액상 고분자형 폴리아인산염 중합체 안정화제 - Google Patents

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Publication number

KR101377467B1

KR101377467B1 KR1020127021440A KR20127021440A KR101377467B1 KR 101377467 B1 KR101377467 B1 KR 101377467B1 KR 1020127021440 A KR1020127021440 A KR 1020127021440A KR 20127021440 A KR20127021440 A KR 20127021440A KR 101377467 B1 KR101377467 B1 KR 101377467B1

Authority

KR

South Korea

Prior art keywords

alkyl

group

tert

polyphosphite

butyl

Prior art date

2010-02-19

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• 229920000642 polymer Polymers 0.000 title claims abstract description 62
• 239000007788 liquid Substances 0.000 title claims abstract description 29
• 239000003381 stabilizer Substances 0.000 title description 22
• -1 alkyl glycol ether Chemical compound 0.000 claims abstract description 135
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
• 239000000126 substance Substances 0.000 claims abstract description 12
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
• 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 7
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 38
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 24
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 19
• WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 claims description 19
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 16
• 229920001451 polypropylene glycol Polymers 0.000 claims description 15
• 150000001412 amines Chemical class 0.000 claims description 13
• 229910019142 PO4 Inorganic materials 0.000 claims description 12
• 229920001223 polyethylene glycol Polymers 0.000 claims description 10
• 239000000654 additive Substances 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 9
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 9
• 239000010452 phosphate Substances 0.000 claims description 9
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
• 150000002596 lactones Chemical class 0.000 claims description 7
• 125000001931 aliphatic group Chemical group 0.000 claims description 6
• 229920001515 polyalkylene glycol Polymers 0.000 claims description 6
• 239000004611 light stabiliser Substances 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 239000002202 Polyethylene glycol Substances 0.000 claims description 3
• 230000000996 additive effect Effects 0.000 claims description 3
• 229910052751 metal Inorganic materials 0.000 claims description 3
• 239000002184 metal Substances 0.000 claims description 3
• 150000002989 phenols Chemical class 0.000 claims description 3
• 230000006641 stabilisation Effects 0.000 claims description 3
• 238000011105 stabilization Methods 0.000 claims description 3
• 150000007970 thio esters Chemical class 0.000 claims description 3
• 238000004383 yellowing Methods 0.000 claims description 3
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 4
• 150000001565 benzotriazoles Chemical class 0.000 claims 2
• QVLTXCYWHPZMCA-UHFFFAOYSA-N po4-po4 Chemical compound OP(O)(O)=O.OP(O)(O)=O QVLTXCYWHPZMCA-UHFFFAOYSA-N 0.000 claims 1
• OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract description 20
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
• 238000013508 migration Methods 0.000 abstract description 2
• 230000005012 migration Effects 0.000 abstract description 2
• 239000000203 mixture Substances 0.000 description 70
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 63
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 59
• 229910052757 nitrogen Chemical group 0.000 description 47
• 229920001577 copolymer Polymers 0.000 description 46
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 34
• HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 34
• 239000000047 product Substances 0.000 description 19
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• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
• 239000005977 Ethylene Substances 0.000 description 16
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• 238000006243 chemical reaction Methods 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 239000004952 Polyamide Substances 0.000 description 12
• 239000004700 high-density polyethylene Substances 0.000 description 12
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 12
• 229920002647 polyamide Polymers 0.000 description 12
• 239000012043 crude product Substances 0.000 description 11
• 150000002009 diols Chemical class 0.000 description 11
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• 239000011368 organic material Substances 0.000 description 11
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• 125000000623 heterocyclic group Chemical group 0.000 description 10
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• HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 10
• 239000005062 Polybutadiene Substances 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 238000001125 extrusion Methods 0.000 description 9
• 239000007789 gas Substances 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
• 235000021317 phosphate Nutrition 0.000 description 9
• 239000004417 polycarbonate Substances 0.000 description 9
• 229920002554 vinyl polymer Polymers 0.000 description 9
• KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
• GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 8
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
• 235000013305 food Nutrition 0.000 description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• 238000012545 processing Methods 0.000 description 8
• 239000003963 antioxidant agent Substances 0.000 description 7
• 235000006708 antioxidants Nutrition 0.000 description 7
• 235000013539 calcium stearate Nutrition 0.000 description 7
• 239000008116 calcium stearate Substances 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 7
• 239000000835 fiber Substances 0.000 description 7
• 229910052736 halogen Inorganic materials 0.000 description 7
• 150000002367 halogens Chemical class 0.000 description 7
• 239000000178 monomer Substances 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 229920005989 resin Polymers 0.000 description 7
• 239000011347 resin Substances 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
• BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
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• 150000002148 esters Chemical class 0.000 description 6
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• 239000007983 Tris buffer Substances 0.000 description 5
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• 238000004458 analytical method Methods 0.000 description 5
• 230000003078 antioxidant effect Effects 0.000 description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
• 230000015556 catabolic process Effects 0.000 description 5
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• WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
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